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Noncovalent Organocatalytic Synthesis of Enantioenriched Terminal Aziridines with a Quaternary Stereogenic Center

Author:
De Fusco, Claudia, Fuoco, Tiziana, Croce, Gianluca, Lattanzi, Alessandra
Source:
Organic letters 2012 v.14 no.16 pp. 4078-4081
ISSN:
1523-7052
Subject:
acrylates, amino acids, chemical reactions, chemical structure, enantioselectivity, esters, ethyleneimine, regioselectivity, thiourea
Abstract:
A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of α-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable α,α-disubstituted α-amino acid esters has been demonstrated.
Agid:
5784186